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Welcome to Crowley County, named in honor of State Senator John H. Crowley.  It was created May 29, 1911 out of part of Otero and Kiowa counties.  Previously both were parts of Bent County.  The first significant development and settlement occurred in 1887 when the Missouri Pacific Railroad came through from the east on its way to Pueblo and Colorado's gold fields.  Crowley County's seat of government Ordway, a town established in 1890 that quickly became the economic hub of the area. Other towns are Sugar City (est. 1891), Crowley (originally called Bradbury, 1880), and Olney Springs (est. 1887).

A few years later, developers brought a canal east from the Arkansas River, with ambitious plans to irrigate a million acres in Kansas; instead, the canal tapered off in Crowley County but did it irrigate 57,000 acres along its length. This turned early Crowley County into a lush agricultural mecca but by the 1970s almost all the water rights were sold to the fast-growing cities of Colorado's Front Range corridor. The area's economic activity shifted toward ranching and much of the land returned to its original sparse prairie grassland conditions.

Today Crowley County hosts a state prison. The 2000 census showed 5,518 county residents, of which 1,955 were prisoners, giving Crowley County the highest percentage of incarcerated prisoners of any county in the U.S.